The amide group of the title compound, C
7H
5Cl
2NO, forms a dihedral angle of 76.64 (5)° with the plane of the benzene ring. In the crystal structure, intermolecular N—H
Cl and N—H
O hydrogen bonds link molecules, forming one-dimensional chains in the
c-axis direction.
Supporting information
CCDC reference: 295948
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean (C-C)= 0.002 Å
- R factor = 0.030
- wR factor = 0.078
- Data-to-parameter ratio = 14.3
checkCIF/PLATON results
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Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-Plus (Sheldrick, 1991) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.
2,6-dichlorobenzamide
top
Crystal data top
C7H5Cl2NO | Dx = 1.524 Mg m−3 |
Mr = 190.02 | Melting point: 196 K |
Orthorhombic, Pbcn | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2n 2ab | Cell parameters from 17745 reflections |
a = 12.7941 (9) Å | θ = 3.5–25.8° |
b = 13.5868 (8) Å | µ = 0.72 mm−1 |
c = 9.5283 (6) Å | T = 173 K |
V = 1656.31 (18) Å3 | Needle, colorless |
Z = 8 | 0.42 × 0.20 × 0.20 mm |
F(000) = 768 | |
Data collection top
Stoe IPDS-II two-circle diffractometer | 1556 independent reflections |
Radiation source: fine-focus sealed tube | 1486 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.056 |
ω scans | θmax = 25.6°, θmin = 3.7° |
Absorption correction: multi-scan (MULABS; Spek, 2003; Blessing, 1995) | h = −15→15 |
Tmin = 0.752, Tmax = 0.869 | k = −16→13 |
16372 measured reflections | l = −11→11 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.030 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.078 | w = 1/[σ2(Fo2) + (0.0334P)2 + 0.9959P] where P = (Fo2 + 2Fc2)/3 |
S = 1.11 | (Δ/σ)max = 0.001 |
1556 reflections | Δρmax = 0.30 e Å−3 |
109 parameters | Δρmin = −0.38 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0098 (13) |
Special details top
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The threshold expression of F2 >
σ(F2) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F2 are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Cl1 | 0.66990 (3) | 0.47318 (4) | 0.64618 (5) | 0.04017 (18) | |
Cl2 | 0.84012 (4) | 0.74376 (4) | 0.29460 (6) | 0.0488 (2) | |
N1 | 0.88652 (12) | 0.50808 (11) | 0.38477 (15) | 0.0299 (3) | |
H1A | 0.8503 (17) | 0.4998 (18) | 0.304 (3) | 0.044 (6)* | |
H1B | 0.9486 (19) | 0.4821 (16) | 0.387 (2) | 0.040 (6)* | |
O1 | 0.90267 (8) | 0.57900 (8) | 0.59937 (11) | 0.0256 (3) | |
C1 | 0.74694 (11) | 0.61229 (10) | 0.46944 (14) | 0.0198 (3) | |
C2 | 0.65837 (11) | 0.57668 (12) | 0.53862 (16) | 0.0232 (3) | |
C3 | 0.56070 (13) | 0.62076 (13) | 0.52519 (17) | 0.0320 (4) | |
H3 | 0.5019 | 0.5949 | 0.5737 | 0.038* | |
C4 | 0.55038 (14) | 0.70310 (14) | 0.43974 (19) | 0.0366 (4) | |
H4 | 0.4840 | 0.7337 | 0.4297 | 0.044* | |
C5 | 0.63597 (16) | 0.74096 (12) | 0.3691 (2) | 0.0356 (4) | |
H5 | 0.6286 | 0.7972 | 0.3107 | 0.043* | |
C6 | 0.73298 (13) | 0.69567 (12) | 0.38470 (16) | 0.0274 (4) | |
C7 | 0.85294 (11) | 0.56459 (11) | 0.48903 (15) | 0.0200 (3) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.0313 (3) | 0.0482 (3) | 0.0410 (3) | −0.01246 (18) | −0.01176 (18) | 0.0246 (2) |
Cl2 | 0.0492 (3) | 0.0509 (3) | 0.0464 (3) | −0.0158 (2) | −0.0061 (2) | 0.0268 (2) |
N1 | 0.0265 (7) | 0.0407 (8) | 0.0226 (7) | 0.0103 (6) | −0.0081 (6) | −0.0109 (6) |
O1 | 0.0245 (6) | 0.0339 (6) | 0.0184 (5) | 0.0043 (4) | −0.0062 (4) | −0.0034 (5) |
C1 | 0.0250 (7) | 0.0199 (7) | 0.0145 (6) | 0.0011 (6) | −0.0065 (6) | −0.0030 (5) |
C2 | 0.0255 (8) | 0.0267 (8) | 0.0174 (7) | −0.0004 (6) | −0.0070 (6) | 0.0002 (6) |
C3 | 0.0240 (8) | 0.0446 (10) | 0.0275 (8) | 0.0028 (7) | −0.0056 (7) | −0.0068 (7) |
C4 | 0.0327 (9) | 0.0386 (10) | 0.0384 (9) | 0.0155 (8) | −0.0140 (8) | −0.0105 (8) |
C5 | 0.0486 (11) | 0.0225 (8) | 0.0358 (10) | 0.0094 (7) | −0.0188 (8) | −0.0010 (7) |
C6 | 0.0355 (9) | 0.0226 (8) | 0.0242 (7) | −0.0016 (6) | −0.0081 (7) | 0.0026 (6) |
C7 | 0.0221 (7) | 0.0202 (7) | 0.0178 (7) | −0.0016 (5) | −0.0024 (5) | 0.0016 (6) |
Geometric parameters (Å, º) top
Cl1—C2 | 1.7463 (16) | C1—C7 | 1.515 (2) |
Cl2—C6 | 1.7444 (18) | C2—C3 | 1.392 (2) |
N1—C7 | 1.327 (2) | C3—C4 | 1.390 (3) |
N1—H1A | 0.91 (2) | C3—H3 | 0.9500 |
N1—H1B | 0.87 (2) | C4—C5 | 1.384 (3) |
O1—C7 | 1.2444 (18) | C4—H4 | 0.9500 |
C1—C2 | 1.397 (2) | C5—C6 | 1.393 (2) |
C1—C6 | 1.403 (2) | C5—H5 | 0.9500 |
| | | |
C7—N1—H1A | 122.8 (14) | C5—C4—C3 | 120.58 (15) |
C7—N1—H1B | 120.7 (14) | C5—C4—H4 | 119.7 |
H1A—N1—H1B | 116 (2) | C3—C4—H4 | 119.7 |
C2—C1—C6 | 116.61 (14) | C4—C5—C6 | 119.25 (16) |
C2—C1—C7 | 121.32 (13) | C4—C5—H5 | 120.4 |
C6—C1—C7 | 122.04 (14) | C6—C5—H5 | 120.4 |
C3—C2—C1 | 122.40 (15) | C5—C6—C1 | 122.11 (16) |
C3—C2—Cl1 | 118.45 (13) | C5—C6—Cl2 | 118.82 (13) |
C1—C2—Cl1 | 119.16 (11) | C1—C6—Cl2 | 119.07 (13) |
C4—C3—C2 | 119.05 (16) | O1—C7—N1 | 123.92 (14) |
C4—C3—H3 | 120.5 | O1—C7—C1 | 119.64 (13) |
C2—C3—H3 | 120.5 | N1—C7—C1 | 116.44 (13) |
| | | |
C6—C1—C2—C3 | 0.1 (2) | C4—C5—C6—Cl2 | 179.74 (13) |
C7—C1—C2—C3 | 178.30 (14) | C2—C1—C6—C5 | −0.3 (2) |
C6—C1—C2—Cl1 | −179.90 (11) | C7—C1—C6—C5 | −178.51 (14) |
C7—C1—C2—Cl1 | −1.66 (19) | C2—C1—C6—Cl2 | −179.72 (11) |
C1—C2—C3—C4 | 0.1 (2) | C7—C1—C6—Cl2 | 2.06 (19) |
Cl1—C2—C3—C4 | −179.90 (12) | C2—C1—C7—O1 | −75.45 (19) |
C2—C3—C4—C5 | −0.1 (2) | C6—C1—C7—O1 | 102.70 (17) |
C3—C4—C5—C6 | −0.1 (3) | C2—C1—C7—N1 | 103.92 (17) |
C4—C5—C6—C1 | 0.3 (2) | C6—C1—C7—N1 | −77.94 (19) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···Cl1i | 0.91 (2) | 2.78 (2) | 3.5936 (15) | 150.4 (18) |
N1—H1A···O1i | 0.91 (2) | 2.32 (2) | 2.9728 (18) | 128.5 (18) |
N1—H1B···O1ii | 0.87 (2) | 2.08 (2) | 2.9491 (18) | 178 (2) |
Symmetry codes: (i) x, −y+1, z−1/2; (ii) −x+2, −y+1, −z+1. |